CN109679374B - Yellow disperse dye composition, disperse dye, and preparation method and application thereof - Google Patents
Yellow disperse dye composition, disperse dye, and preparation method and application thereof Download PDFInfo
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- CN109679374B CN109679374B CN201811574826.3A CN201811574826A CN109679374B CN 109679374 B CN109679374 B CN 109679374B CN 201811574826 A CN201811574826 A CN 201811574826A CN 109679374 B CN109679374 B CN 109679374B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0079—Azoic dyestuff preparations
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/008—Preparations of disperse dyes or solvent dyes
- C09B67/0082—Preparations of disperse dyes or solvent dyes in liquid form
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Abstract
The invention relates to a yellow disperse dye composition, a disperse dye, a preparation method and application thereof. The disperse dye is suitable for dyeing terylene and blended fabrics thereof. The yellow disperse dye composition has high strength and low cost; the dyed fabric has good sublimation fastness and washing fastness; has high compatibility and wide pH value range.
Description
Technical Field
The invention relates to a yellow disperse dye composition, a disperse dye and a preparation method thereof, and also relates to the dyeing application of the yellow disperse dye composition and the disperse dye to fabrics, fabrics obtained by dyeing with the yellow disperse dye composition and the disperse dye and fabric products made of the fabrics. The disperse dye is more suitable for dyeing terylene and blended fabrics thereof from yellow to golden yellow.
Background
Aniline is one of the most basic chemical raw materials, but is often incompletely synthesized, has a large amount of residues, and has great harm to the health of human bodies and the environment. The international cancer research organization of world health organization in 10 months in 2017 lists aniline in 3 carcinogenic lists, the STANDARD 100by OEKO-TEX in 2018 lists aniline in carcinogenic aromatic amine and carries out limit requirement on the aniline, and the countries also strictly control aniline in printing and dyeing sewage. The development of the environment-friendly dye is the most important thing in the enterprises at present, is an urgent matter, and is the fundamental place about the sustainable development of the enterprises.
The environment-friendly yellow dye fish dragon in the current market is mixed, but has certain defects, such as high price, general compatibility, poor fastness and the like. Zhejiang leata gmbh has introduced disperse dye in CN102924975B in 2012, and although the price is lower than that of quinoline yellow environment-friendly dye, the sublimation fastness is general, and the product application is limited, and the product popularization and application are more limited in 2018 due to the problem of aniline. In order to overcome the problem, a yellow disperse dye composition which is higher in cost performance, better in performance and more environment-friendly is provided.
Disclosure of Invention
The invention provides a yellow disperse dye composition with higher cost performance, better performance and more environmental protection, and particularly the sublimation fastness is greatly improved.
Means for solving the problems
The invention provides a disperse dye composition, which consists of the following components:
one or two components A shown in a formula (1),
in the formula (1), the reaction mixture is,
R1is methyl or ethyl; and
one or more than two components B shown in a formula (2),
in the formula (2), the reaction mixture is,
X1、X2each independently is hydrogen, nitro, cyano or halogen atom; r2、R3Each independently is C1～C4The substituent is-OCOR4、-COOR5、-CH＝CH2、-CN、-OCO-Ph、-OCH2CH2CN or-Ph, wherein R4、R5Each independently is C1～C4When X is alkyl, and1、X2simultaneously being hydrogen, R2is-CH2CH2When CN, R3Is not-CH2Ph (i.e. excluding the present application)Please refer to the compound of formula (5).
According to the disperse dye composition, the component A is one or two of the following compounds:
according to the disperse dye composition, the component B is one or more than two of the following compounds:
the disperse dye composition comprises the following components in percentage by weight based on the total weight of the disperse dye composition:
35 to 99 percent by weight, preferably 50 to 95 percent by weight of component A,
1-65% by weight, preferably 5-50% by weight of component B.
In practice, the dye components of the present invention may often carry some by-products and other impurities without affecting the practice of the present invention.
The invention also provides a disperse dye, which comprises the disperse dye composition and auxiliary materials; preferably, the auxiliary materials comprise an auxiliary agent and water; more preferably, the adjuvant comprises one or a combination of two or more of a surfactant, a bactericide or a dye dispersant.
According to the disperse dye, the dye dispersant comprises one or more of the following combinations: naphthalene sulfonic acid formaldehyde condensates (e.g., dispersant MF, dispersant CNF, dispersant NNO), lignosulfonates (e.g., lignin 85A, lignin 83A), or anhydrous sodium sulphate.
According to the disperse dye, the weight ratio of the auxiliary agent to the disperse dye composition is 0.2-6: 1; preferably, the disperse dye is liquid after being ground by a sand mill or a grinding machine, and the solid content is 20-50%, or the disperse dye is powdery or granular after being spray-dried, and the solid content is 87-96%.
The invention also provides a method for preparing the disperse dye, which comprises the following steps:
mixing the dye components, and then carrying out granulation treatment by using a sand mill or a grinding machine in the presence of auxiliary materials; or granulating the dye components by a sand mill or a grinding machine in the presence of auxiliary materials, and mixing.
The invention also provides the use of the disperse dyes according to the invention for dyeing textiles; preferably, the fabric is terylene and blended fabric thereof.
The invention also provides a fabric prepared by dyeing with the disperse dye; preferably, the fabric is terylene and blended fabric thereof.
ADVANTAGEOUS EFFECTS OF INVENTION
The disperse dye is very suitable for dyeing terylene and blended fabrics thereof, has bright color, high cost performance, strong environmental protection, higher compatibility and wider pH value adaptation range, has good fastness, and particularly has obvious advantages in sublimation fastness and washing fastness.
Detailed Description
The present invention is further illustrated by the following examples, but the scope of the invention is not limited thereto.
In the embodiment, the component A and the component B are mixed with the auxiliary agent and water according to a certain proportion, and then are ground and dispersed by a sand mill to prepare slurry, or are further spray-dried to prepare the dye.
The components A and B are known dye compounds and are commercially available or can be prepared by existing methods.
The preparation or source of the specific compounds used in the examples are as follows.
The compound of formula (1-1) is c.i. disperse yellow 241 produced by zhejiang leata gmbh.
A process for producing a compound of formula (1-2): 3, 4-dichloroaniline is diazotized and coupled with N-ethyl-3-cyano-4-methyl-6-hydroxy-2-pyridone.
The compound of formula (2-1) is c.i. disperse orange 25 manufactured by zhejiang leata gmbh.
The compound of formula (2-2) is c.i. disperse orange 31 produced by zhejiang leata gmbh.
The compound of formula (2-3) is c.i. disperse orange 25 produced by zhejiang leata gmbh: 1.
the compound of formula (2-4) is c.i. disperse orange 73 produced by zhejiang leata gmbh.
A process for producing a compound of formula (2-5): diazotizing p-nitroaniline and coupling with N, N-dicyanoethylaniline.
A process for producing a compound of formula (2-6): diazotizing 2, 6-dichloro-4-nitroaniline and coupling with N-methyl-N-benzyl.
The compound of formula (2-7) is c.i. disperse orange 80 produced by zhejiang leata gmbh.
Example 1
73.1 g of the compound of the formula (1-1), 26.9 g of the compound of the formula (2-1), 100 g of lignin 85A, 200 g of the dispersant MF and 100 g of the dispersant NNO are added with 750 g of water and fully stirred uniformly, ground, dispersed and dried to obtain the yellow disperse dye.
Comparative example 1
The procedure of example 1 was repeated, except that the compound of formula (1-1) of example 1 was replaced with a compound of the following formula (3).
The yellow disperse dyes of example 1 and comparative example 1 were subjected to a performance test.
The specific test method is as follows:
1.0 g of the yellow disperse dyes of example 1 and comparative example 1 were weighed in 500ml of water, respectively, to prepare a disperse dye suspension. Absorbing 40ml of disperse dye suspension, mixing with 60ml of water, adjusting the pH value of a dye bath to 5 by using acetic acid, then heating to 60 ℃, simultaneously respectively adding 2g of polyester fiber for high-temperature high-pressure dyeing, heating to 130 ℃ within 35 minutes, preserving heat for 45 minutes, cooling to 80 ℃ and sampling. The intensity was measured by the same dyeing method, using 1% dye.
The sublimation fastness, aniline content and strength of the fiber are measured according to GB/T5718-1997, EN ISO14362-1:2017 and GB/T6688-2008, and the test results are shown in Table 1.
TABLE 1
| Name of the embodiment | Fastness to sublimation | Aniline (mg/kg) | Strength of |
| Example 1 | 3 | <5 | 104％ |
| Comparative example 1 | 2 | 375 | 100％ |
Note: the minimum aniline content of the STANDARD 100by OEKO-TEX on the textile is less than or equal to 100 mg/kg.
Example 2
79 g of the compound of the formula (1-2), 21 g of the compound of the formula (2-2), 119 g of lignin 85A and 119 g of a dispersant MF are added with 550 g of water and stirred uniformly, ground, dispersed and dried to obtain a yellow disperse dye.
Comparative example 2
The procedure of example 2 was repeated, except that the compound of formula (1-2) of example 2 was replaced with the compound of formula (4) below, otherwise unchanged.
The yellow disperse dyes of example 2 and comparative example 2 were subjected to a performance test.
The specific test method is as follows:
1.0 g of the yellow disperse dyes of example 2 and comparative example 2 were weighed in 500ml of water, respectively, to prepare a disperse dye suspension. Absorbing 40ml of disperse dye suspension, mixing with 60ml of water, adjusting the pH value of a dye bath to 5 by using acetic acid, then heating to 60 ℃, simultaneously respectively adding 2g of polyester fiber for high-temperature high-pressure dyeing, heating to 130 ℃ within 35 minutes, preserving heat for 45 minutes, cooling to 80 ℃ and sampling.
The washing fastness is determined according to GB/T3921-2008, and the test results are shown in Table 2.
TABLE 2
| Name of the embodiment | Fastness to washing |
| Example 2 | 5 |
| Comparative example 2 | 4 |
And because the prices of the quinolines are higher, the cost of the embodiment 2 is about 30 percent lower than that of the comparison 2, and the quinoline has more market competitiveness.
Example 3
52 g of the compound of the formula (1-1), 48 g of the compound of the formula (2-1) and 488 g of a diffusant NNO are added with 900 g of water and stirred uniformly, ground, dispersed and dried to obtain the golden yellow disperse dye.
Comparative example 3
The procedure of example 3 was repeated, except that the compound of formula (2-1) of example 3 was replaced with the compound of formula (5) below, otherwise unchanged.
The golden yellow disperse dyes of example 3 and comparative example 3 were subjected to a performance test.
The specific test method is as follows:
1.0 g of the gold disperse dyes of example 3 and comparative example 3 were weighed in 500ml of water, respectively, to prepare a disperse dye suspension. 10ml of disperse dye suspension is sucked and mixed with 90ml of water, the pH value of a dye bath is adjusted to 5 by using acetic acid, then the temperature is raised to 60 ℃, 2g of polyester fiber is respectively added for high-temperature high-pressure dyeing, the temperature is raised to 130 ℃ within 35 minutes, the temperature is kept for 45 minutes, and the sample is taken after being cooled to 80 ℃.
The light fastness was determined according to GB/T8427-2008, the test results are shown in Table 3.
TABLE 3
| Name of the embodiment | Color fastness to sunlight |
| Examples3 | 7 |
| Comparative example 3 | 6 |
Example 4
55 g of the compound of the formula (1-1), 15 g of the compound of the formula (2-1) and 190 g of lignin 83A are added with 390 g of water and stirred uniformly, ground, dispersed and dried to obtain yellow disperse dye.
Comparative example 4
The procedure of example 4 was repeated except for adding 390 g of water to 55 g of the compound of the formula (1-1), 10 g of the compound of the formula (2-1), 5 g of the compound of the formula (5) in comparative example 3 and 190 g of lignin 83A, followed by stirring well, followed by grinding, dispersion and drying to obtain a yellow disperse dye.
The yellow disperse dyes of example 4 and comparative example 4 were subjected to a performance test.
The specific test method is as follows:
1.0 g of the yellow disperse dyes of example 4 and comparative example 4 were weighed in 500ml of water, respectively, to prepare a disperse dye suspension. 10ml of disperse dye suspension is sucked and mixed with 90ml of water, the pH value of a dye bath is adjusted to 5 by using acetic acid, then the temperature is raised to 60 ℃, 2g of polyester fiber is respectively added for high-temperature high-pressure dyeing, the temperature is raised to 130 ℃ within 35 minutes, the temperature is kept for 45 minutes, and the sample is taken after being cooled to 80 ℃.
The light fastness was determined according to GB/T8427-2008, and the test results are shown in Table 4.
TABLE 4
| Name of the embodiment | Color fastness to sunlight |
| Example 4 | 7 |
| Comparative example 4 | 6-7 |
Examples 5 to 13
The yellow disperse dyes were prepared by mixing component a, component B, the auxiliaries with water, grinding, and making liquid dyes or spray drying according to table 5.
Table 5 units: keke (Chinese character of 'Keke')
Note: water in table 5 is the moisture content of the final commercial product.
1.0 g of the disperse dyes prepared in examples 5 to 13 were placed in 500ml of water to prepare disperse dye suspensions. Absorbing 40ml of disperse dye suspension, mixing with 60ml of water, adjusting the pH value of a dye bath to 5 by using acetic acid, then heating to 60 ℃, simultaneously respectively adding 2g of polyester fiber for high-temperature high-pressure dyeing, heating to 130 ℃ within 35 minutes, preserving heat for 45 minutes, cooling to 80 ℃ and sampling.
The sublimation fastness and washing fastness of the dye are measured according to GB/T5718-1997 and GB/T3921-2008, and the test results are shown in Table 6.
TABLE 6
| Examples | Fastness to sublimation | Fastness to washing |
| 5 | 3 | 5 |
| 6 | 3-4 | 5 |
| 7 | 3 | 5 |
| 8 | 3-4 | 5 |
| 9 | 3 | 5 |
| 10 | 3-4 | 5 |
| 11 | 3 | 5 |
| 12 | 3 | 5 |
| 13 | 3-4 | 5 |
As can be seen from Table 6, the sublimation fastness and washing fastness of examples 5 to 13 are good.
Claims (14)
1. A disperse dye composition is characterized by comprising the following components:
one or two components A shown in a formula (1),
in the formula (1), the reaction mixture is,
R1is methyl or ethyl; and
one or more than two components B shown in formulas (2-1) to (2-7),
the disperse dye composition comprises the following components in percentage by weight based on the total weight of the disperse dye composition:
35 to 99 percent of the component A by weight percentage,
1-65% by weight of component B.
2. The disperse dye composition according to claim 1, wherein the component A is one or two of the following compounds:
3. the disperse dye composition according to claim 1 or 2, characterized by consisting of, based on the total weight of the disperse dye composition:
50-95 wt% of component A,
5-50% of component B.
4. A disperse dye, comprising the disperse dye composition according to any one of claims 1 to 3 and an auxiliary material.
5. A disperse dye according to claim 4, wherein the auxiliary materials comprise auxiliaries and water.
6. The disperse dye according to claim 5, wherein the auxiliary agent comprises one or a combination of two or more of a surfactant, a bactericide or a dye dispersant.
7. The disperse dye according to claim 6, wherein the dye dispersant comprises one or a combination of two or more of the following: naphthalene sulfonic acid formaldehyde condensates, lignosulfonates, or anhydrous sodium sulfate.
8. A disperse dye according to any one of claims 5 to 7, wherein the weight ratio of the auxiliary agent to the disperse dye composition is 0.2 to 6: 1.
9. A disperse dye according to claim 8, wherein the disperse dye is liquid after being ground by a sand mill or a grinder and has a solid content of 20 to 50%, or the disperse dye is powdery or granular after being spray-dried and has a solid content of 87 to 96%.
10. A process for preparing a disperse dye according to any one of claims 4 to 9, comprising the steps of:
mixing the dye components, and then carrying out granulation treatment by using a sand mill or a grinding machine in the presence of auxiliary materials; or granulating the dye components by a sand mill or a grinding machine in the presence of auxiliary materials, and mixing.
11. Use of a disperse dye according to any one of claims 4 to 9 for dyeing textiles.
12. Use according to claim 11, characterized in that the fabric is dacron and its blend fabrics.
13. A fabric prepared by dyeing with the disperse dye according to any one of claims 4 to 9.
14. The fabric of claim 13, wherein the fabric is a polyester or blend thereof.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201811574826.3A CN109679374B (en) | 2018-12-21 | 2018-12-21 | Yellow disperse dye composition, disperse dye, and preparation method and application thereof |
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| CN201811574826.3A CN109679374B (en) | 2018-12-21 | 2018-12-21 | Yellow disperse dye composition, disperse dye, and preparation method and application thereof |
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| CN109679374B true CN109679374B (en) | 2021-05-11 |
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| CN114085548B (en) * | 2021-11-25 | 2023-07-28 | 约克夏(浙江)染化有限公司 | Orange disperse dye composition, orange disperse dye, and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| ES2315655T3 (en) * | 2003-04-22 | 2009-04-01 | Huntsman Advanced Materials (Switzerland) Gmbh | PIGMENT / COLORING BLENDS. |
| CN100543087C (en) * | 2007-02-14 | 2009-09-23 | 浙江龙盛染料化工有限公司 | A kind of disperse azo dye composition |
| CN101412857B (en) * | 2008-11-26 | 2011-12-21 | 浙江闰土股份有限公司 | Environment-friendly yellow disperse dye composition |
| CN101760045B (en) * | 2009-12-30 | 2013-07-24 | 浙江闰土股份有限公司 | Medium-low temperature environmental-friendly disperse dye composition |
| CN102924975B (en) * | 2012-11-12 | 2014-09-10 | 浙江闰土股份有限公司 | Disperse dye composition and disperse dyes, and preparation method and purpose thereof |
| CN103450708B (en) * | 2013-09-10 | 2015-02-25 | 江苏亚邦染料股份有限公司 | Environment-friendly orange disperse dye mixture |
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Effective date of registration: 20221116 Address after: 312369 No.1, Weiqi East Road, Shangyu economic and Technological Development Zone, Hangzhou Bay, Shaoxing City, Zhejiang Province Patentee after: ZHEJIANG RUNTU Co.,Ltd. Patentee after: Yorkshire (Zhejiang) Dyeing and Chemical Co.,Ltd. Address before: 312368, Shangyu Road, Shaoxing, Zhejiang Province Patentee before: ZHEJIANG RUNTU Co.,Ltd. |